For research use only. Not for therapeutic Use.
Acivicin（Cat No.:R047710）is a natural glutamine analog with antitumor and antimicrobial properties, derived from the bacterium Streptomyces sviceus. It acts as an irreversible inhibitor of glutamine-dependent enzymes, such as gamma-glutamyl transpeptidase and carbamoyl phosphate synthetase, disrupting nucleotide and amino acid biosynthesis. Acivicin has shown promise in preclinical studies for cancer treatment by targeting metabolic pathways crucial for tumor growth. Additionally, it is used as a research tool to study enzyme functions and metabolic processes. Its unique mechanism highlights its potential in both therapeutic and biochemical research applications.
| Catalog Number | R047710 |
| CAS Number | 42228-92-2 |
| Synonyms | (αS,5S)-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid; [S-(R*,R*)]-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid; AT 125; Antibiotic AT 125; NSC 163501; U 42126; (+)-Acivicin |
| Molecular Formula | C5H7ClN2O3 |
| Purity | ≥95% |
| Storage | -20°C |
| IUPAC Name | (2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid |
| InChI | InChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1 |
| InChIKey | QAWIHIJWNYOLBE-OKKQSCSOSA-N |
| SMILES | C1[C@H](ON=C1Cl)[C@@H](C(=O)O)N |
| Reference | </br>1:An Improved Model of the Trypanosoma brucei CTP Synthetase Glutaminase Domain-Acivicin Complex. Oliveira de Souza J, Dawson A, Hunter WN.ChemMedChem. 2017 Apr 20;12(8):577-579. doi: 10.1002/cmdc.201700118. Epub 2017 Mar 31. PMID: 28333400 Free PMC Article</br>2:High Resolution X-ray Diffraction Dataset for Bacillus licheniformis Gamma Glutamyl Transpeptidase-acivicin complex: SUMO-Tag Renders High Expression and Solubility. Kumari S, Pal RK, Gupta R, Goel M.Protein J. 2017 Feb;36(1):7-16. doi: 10.1007/s10930-017-9693-2. PMID: 28120227 </br>3:Characterization of the acivicin effects on trichothecene production by Fusarium graminearum species complex. Maeda K, Nakajima Y, Tanahashi Y, Kosaki T, Kitou Y, Kanamaru K, Kobayashi T, Nishiuchi T, Kimura M.J Gen Appl Microbiol. 2016 Nov 25;62(5):272-276. Epub 2016 Sep 6. No abstract available. PMID: 27600357 Free Article</br>4:Target discovery of acivicin in cancer cells elucidates its mechanism of growth inhibition†Electronic supplementary information (ESI) available: Synthesis, cloning, protein expression, purification and biochemical assays. See DOI: 10.1039/c4sc02339k. Kreuzer J, Bach NC, Forler D, Sieber SA.Chem Sci. 2014 Dec 1;6(1):237-245. Epub 2014 Sep 26. PMID: 25580214 Free PMC Article</br>5:Effects of acivicin on growth, mycotoxin production and virulence of phytopathogenic fungi. Maeda K, Nakajima Y, Motoyama T, Kitou Y, Kosaki T, Saito T, Nishiuchi T, Kanamaru K, Osada H, Kobayashi T, Kimura M.Lett Appl Microbiol. 2014 Oct;59(4):377-83. doi: 10.1111/lam.12289. Epub 2014 Jun 19. PMID: 24863673 </br>6:Structure of Bacillus subtilis γ-glutamyltranspeptidase in complex with acivicin: diversity of the binding mode of a classical and electrophilic active-site-directed glutamate analogue. Ida T, Suzuki H, Fukuyama K, Hiratake J, Wada K.Acta Crystallogr D Biol Crystallogr. 2014 Feb;70(Pt 2):607-14. doi: 10.1107/S1399004713031222. Epub 2014 Jan 31. PMID: 24531494 Free PMC Article</br>7:The biological targets of acivicin inspired 3-chloro- and 3-bromodihydroisoxazole scaffolds. Orth R, Böttcher T, Sieber SA.Chem Commun (Camb). 2010 Nov 28;46(44):8475-7. doi: 10.1039/c0cc02825h. Epub 2010 Oct 8. PMID: 20936198 </br>8:Crystal structure of acivicin-inhibited gamma-glutamyltranspeptidase reveals critical roles for its C-terminus in autoprocessing and catalysis. Williams K, Cullati S, Sand A, Biterova EI, Barycki JJ.Biochemistry. 2009 Mar 24;48(11):2459-67. doi: 10.1021/bi8014955. PMID: 19256527 Free PMC Article</br>9:Acivicin with glutaminase regulates proliferation and invasion of human MCF-7 and OAW-42 cells–an in vitro study. Roy S, Ghosh S, Mallick P, Maity P.Indian J Exp Biol. 2008 Jan;46(1):22-6. PMID: 18697567 </br>10:Phase II study of acivicin in patients with recurrent high grade astrocytoma. Olver IN, Green M, Millward MJ, Bishop JF.J Clin Neurosci. 1998 Jan;5(1):46-8. PMID: 18644287 |
